Ethyl Acetate → HCID 23387866, Verbindung

HRID 1839347

Reaktionsgleichung

Reaktionsgleichung von HRID 1839347
[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O-:23])=[O:22])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH3:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].[CH3:27][O:28][C:29]1[CH:39]=[CH:38][CH:37]=[CH:36][C:30]=1[C:31]([O:33][CH2:34]Cl)=[O:32].[C:40](OCC)(=O)C>CN(C=O)C.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O:23][CH:34]([O:33][C:31](=[O:32])[C:30]3[CH:36]=[CH:37][CH:38]=[CH:39][C:29]=3[O:28][CH3:27])[CH3:40])=[O:22])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH3:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 234492712-Methoxybenzoyloxymethyl chlorideHCID 23669370Sodium (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-(7-methylthio-imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

Produkt 1

HCID 23387866HCID 23387866, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo[5,1-b]thiazol2-yl)-1-carbapen-2-em-3-carboxylate (170 mg) was dissolved in 2 ml of DMF. Triethylbenzylammonium chloride (193 mg) and 182 mg of 2-methoxybenzoyloxymethyl chloride were added to the solution in an argon atmosphere. The mixture was stirred under ice cooling for 2 hr and then stirred at room temperature for 5 hr. Ethyl acetate (30 ml) was added to the reaction solution. The mixture was washed twice with 20 ml of semisaturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated to a volume of 5 ml under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol=40: 1) to give 131 mg of the title compound.

Aufarbeitung

  1. stirringstirred at room temperature for 5 hr
  2. washThe mixture was washed twice with 20 ml of semisaturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a volume of 5 ml under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane: methanol=40: 1)

Quellen und Nachweise

ORD-Eintrag
ord-969dd61671a94d4e94269ab287b6d977
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677331B2

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